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Arylhydrazone Derivatives of Naproxen As New Analgesic and Anti-Inflammatory Agents: Design, Synthesis and Molecular Docking Studies Publisher Pubmed



Azizian H1 ; Mousavi Z2 ; Faraji H2 ; Tajik M3 ; Bagherzadeh K4 ; Bayat P5 ; Shafiee A3 ; Almasirad A5
Authors
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Authors Affiliations
  1. 1. Department of Medicinal Chemistry, Pharmacy School, International Vice Chancellor Office, Iran University of Medical Sciences, Tehran, Iran
  2. 2. Department of Pharmacology and Toxicology, Faculty of Pharmacy, Pharmaceutical Sciences Branch, Islamic Azad University, Tehran, Iran
  3. 3. Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran
  4. 4. Razi Drug Research Center, Iran University of Medical Sciences, Tehran, Iran
  5. 5. Department of Medicinal Chemistry, Faculty of Pharmacy, Pharmaceutical Sciences Branch, Islamic Azad University, Tehran, 1941933111, Iran

Source: Journal of Molecular Graphics and Modelling Published:2016


Abstract

A series of new arylidenehydrazone derivatives of naproxen were synthesized and evaluated for their analgesic and anti-inflammatory activities. Some of the synthesized analogues showed comparable activities when compared against naproxen for their analgesic and anti-inflammatory properties. 2-(6-methoxy-2-naphthyl)-N′-[(pyridine-4-yl)methylene]propanoic acid hydrazide 4j was found to be the most active analgesic agent. 2-(6-methoxy-2-naphthyl)-N′-[4-nitrobenzylidene]propanoic acid hydrazide 4g showed highest anti-inflammatory activity in comparison to the naproxen. Molecular modeling study of the synthesized compounds suggested that the designed molecules were well located and bound to the COX-1 and COX-2 active sites. Compound 4g showed the highest selectivity for COX-2 (RCOX-2/COX-1 = 1.94) and higher affinity rather than naproxen in COX-2 active site (RCOX-2/naproxen=1.28). Moreover, the structural analyses confirmed that the E-ap rotamer is the preferred structure for the arylidenehydrazone derivatives. © 2016 Elsevier Inc.
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